Crush the Oreo cookies by placing them in a sealed bag and gently using a rolling pin until you have fine crumbs.

Blend by adding the whole milk to your blender first, then add the vanilla ice cream and the crushed Oreo cookies. Blend on high until combined and smooth, about 30 to 45 seconds.

Adjust the thickness by adding more milk if desired, and blend again to reach your preferred consistency.

Serve by pouring the milkshake into tall glasses. Top with whipped cream and drizzle with chocolate syrup, adding an extra Oreo on top for garnish.